Synthesis and Structural Characterization of 1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (6): 697-701. Previous Articles Next Articles

1,5-二甲基-2-(S)-(1′-苯基乙基)-2-氮杂-8-氧杂-双环[3.3.0]辛烷-3,7-二酮的合成及其结构表征

胡炳成^*, 吕春绪

南京理工大学化工学院南京 210094

收稿日期:2003-09-01 修回日期:2003-11-17 接受日期:2003-12-30 发布日期:2022-09-21
通讯作者: ^*E-mail: hubingcheng@yahoo.com

Synthesis and Structural Characterization of 1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione

HU, Bing-Cheng^*, LÜ, Chun-Xu

School of Chemical Engineering, Nanjing University of Science & Technology,Nanjing 210094

Received:2003-09-01 Revised:2003-11-17 Accepted:2003-12-30 Published:2022-09-21

Abstract

1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione was synthesized. The reaction of 2,3-butanedione with malononitrile gave dimethyldicyano-bicyclolactam. Under acidic condition the lactam was hydrolyzed to dimethylbicyclolactone, which was converted with (S)-(-)-(1-phenylethyl)-amine into the target product. Thestructure was characterized by elemental analysis, IR, ¹H NMR and MS spectra. The crystal structure was determined by single-crystal X-ray diffraction analysis. The crystal belongs to monoclinic system with space group P2₁, unit cell dimensions: a=0.8777(18) nm, b=1.0102(2) nm, c=0.9009(18)nm, β=118.75(3)°, V=0.7003(2) nm³, D_c=1.296 g·cm^－3, μ=0.089 mm^－1, F(000)=292, Z=2, R₁=0.0393, wR₂=0.0955.

Key words: dimethyldicyanobicyclolactam, dimethylbicyclolactone, (S)-(－)-(1-phenylethyl)-amine, X-ray diffraction

Cite this article

HU, Bing-Cheng, LÜ, Chun-Xu. Synthesis and Structural Characterization of 1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione[J]. Chinese Journal of Organic Chemistry, 2004, 24(6): 697-701.

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1,5-二甲基-2-(S)-(1′-苯基乙基)-2-氮杂-8-氧杂-双环[3.3.0]辛烷-3,7-二酮的合成及其结构表征

Synthesis and Structural Characterization of 1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione

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